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Cited by 100Synthesis and Properties of Aromatic CompoundsCyclization and Aryne ChemistryOrganic Chemistry Cycloaddition Reactions

Evaluation of Triplet Aromaticity by the Isomerization Stabilization Energy

Zhu, Jun, An, Ke, Schleyer, Paul von Ragué·2013·Organic Letters
DOI 10.1021/ol400908z
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Abstract

The many manifestations of aromaticity have long fascinated both experimentalists and theoreticians. Due to their degenerate half-filled MOs, triplet [n]annulenes with 4n π-electrons are also aromatic, but the degree of their stabilization has been difficult to quantify. The isomerization stabilization energy (ISE) method has been applied to evaluate the triplet aromaticity. The reliability of this approach is indicated by the strong correlation of the ISE results with NICS(1)zz, a magnetic indicator of triplet state aromaticity.

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  • Later theoretical studies supported Baird's rule for both carbocycles and heterocycles.

    “Later theoretical studies supported the proposal, now known as Baird's rule, for both carbocycles and heterocycles.”

    From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [100]

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Authors
Zhu, J., An, K., & Schleyer, P. V. R.
Affiliations
University of Georgia (US)
Corresponding author
Zhu, Jun
ORCID
Venue
Organic Letters
Publisher
American Chemical Society (ACS)
Published
2013-05-02
Volume
15
Issue
10
Pages
2442-2445
ISSN
  • 1523-7052 (ISSN-L)
  • 1523-7060
DOI
10.1021/ol400908z
OpenAlex
W2323886211
Cited by
100
References
3
Citations by year
2026: 8 · 2025: 5 · 2024: 6 · 2023: 8 · 2022: 7 · 2021: 12 · 2020: 4 · 2019: 5 · 2018: 8 · 2017: 9 · 2016: 5 · 2015: 11 · 2014: 12
FWCI
4.25
Type
journal article
Language
en
Open access
closed
Locations
  • Organic Letters (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
  • Physical Sciences › Chemistry › Organic Chemistry › Cyclization and Aryne Chemistry
  • Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Cycloaddition Reactions
Keywords
magnetic properties, π-electron count

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